Methyl Acrylate → HCID 15541758, compound

HRID 47923Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11](=[O:14])[O:12][CH:13]=2)=[CH:5][CH:4]=1.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[NH:10][C:11](=[O:14])[O:12][C:13]=2[CH:16]([CH3:17])[C:15]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(4-Methoxyphenyl)-2-oxo-4-oxazoline (1.00 g), methyl acrylate (0.94 mL) was dissolved in toluene (20 mL) and boron trifluoride etherate (1.31 mL) was added. The obtained mixture was heated to 90° C., and after stirring for 2 h, the solvent was concentrated under reduced pressure to give an oily substance. The obtained oily substance was subjected to silica gel column chromatography and eluted with n-hexane-ethyl acetate (1:1). The solvent was evaporated and the obtained oil was crystallized from ethanol. Isopropyl ether (10 mL) was added and the mixture was stirred at not higher than 5° C. for 1 h. The crystals were collected by filtration and washed with isopropyl ether to give the title compound (0.30 g; yield 20.7%) as gray-white crystals.

Workup

concentrationthe solvent was concentrated under reduced pressure
customto give an oily substance
washeluted with n-hexane-ethyl acetate (1:1)
customThe solvent was evaporated
customthe obtained oil was crystallized from ethanol
additionIsopropyl ether (10 mL) was added
stirringthe mixture was stirred at not higher than 5° C. for 1 h
filtrationThe crystals were collected by filtration
washwashed with isopropyl ether

Sources & evidence

ORD record: ord-18a0fb9907704b8ca0209de196a13a89
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699995B1

Reaction notes

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